When William Mastrosimone was working on the script for the 1992 mini-series "Sinatra," the singer told him a startling tale that involved Joseph Kennedy Sr., JFK, Chicago mob boss Sam Giancana and Judith Exner, Sinatra's girlfriend who was also mistress to both Kennedy and Giancana.
It was a tale of power, sex, murder, intrigue and hubris, the stuff of Greek tragedy, not to mention political and mob legend.
That story was the starting point for a new play, "Ride the Tiger," now in previews, and opening Wednesday, April 3, at New Haven's Long Wharf Theatre.
An earlier version of the work titled "Dirty Business" premiered in Florida in 2008. But Mastrosimone, (off-Broadway's "Extremities," "The Woolgatherer," and "Shivaree" which premiered at Long Wharf in 1983) says this new version steps away from docudrama and refocuses on the psyches of the high-profile characters.
The Long Wharf production stars John Cunningham as the senior Kennedy, Douglas Sills as JFK, Peter Anthony Stewart as Sinatra, Christina Bennett Lind as Exner, and Jordan Lage as Giancana. Artistic director Gordon Edelstein stages the show.
Over a diner breakfast near the meatpacking district where the theater is located, the Trenton, N. J.-born Mastrosimone, 65, talked about gaining Sinatra's trust and his own efforts to fill in the details of the story of how the singer put the Kennedys in contact with Giancana, how the Mafia's efforts in Chicago helped get Kennedy elected, how the Kennedys — once in office — betrayed that favor, and what happened after.
Short, stout and balding Mastrosimone looks like someone who could easily travel in the shadowy circles of power and intrigue, a no-nonsense sideman who would make you feel comfortable sharing a confidence, counsel or a drink.
"I found Sinatra at a time in his life when he was very willing to tell the story," he says sotto voce.
"This was a man who was 77 and he wanted to get things off his chest," says the writer. "Basically Frank was saying that Sam Giancana had the motive, the means and the opportunity to do this."
"This" meaning the 1963 assassination of the president.
The play takes place from 1960 during the presidential campaign through 1962, and presents a motive that allows the audience to project to Dallas in 1963 and imagine that Kennedy's assassin did not act alone.
The connections among the CIA, JFK and the mob is not breaking news. Members of the Giancana family have already recounted their version of the time in "Double Cross: The Explosive, Inside Story of the Mobster Who Controlled America," a 1992 book by Giancana's brother Chuck Giancana and Chuck's son Sam. Giancana's daughter Antoinette also wrote about political and mob ties in the 2005 book "JFK and Sam: The Connection Between the Giancana and the Kennedy Assassinations."
Mastrosimone is working as a dramatist, using information from Sinatra's personal perspective to imagine the behind-the-scenes power plays.
Does he believe that the well-established mob connections led to Kennedy's assassination?
"Yeah," says Mastrosimone.
It started, he says, in 1960 with the senior Kennedy — who made money in the booze business during and after g Prohibition — asking the entertainer, who was a pal to JFK, to lunch.
"Joe said to Frank, 'You know some very unsavory people in Chicago.' He never said, 'Mafia.' Joe asked Frank to go to Chicago to ask Giancana, who was an organized crime figure there, to swing the union vote Jack's way in the election."
"Sinatra went to Giancana and asked him for this personal 'favor' which was the coin of the realm in that world. The assumption was in the end Kennedy would get the labor vote and the mob would have someone in the White House."
But once elected, Kennedy's brother Robert became attorney general and launched a campaign against the Mafia by jailing, indicting and deporting mobsters all around the country.